Deep Hole Holiday Rentals

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Holiday Rentals in Deep Hole

Key West Cottages
Exterior

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (293)
"I love how quiet and relaxing the property was this time of year. Amazing views. I look forward to returning soon!"
The price is S$155
includes taxes & fees
26 Nov - 27 Nov
Key West Cottages
Blufin Bungalows & Marina
On the beach

Blufin Bungalows & Marina

3.0 star property
9.4 out of 10, Exceptional, (83)
"Great stay! Our family had a great time!"
Blufin Bungalows & Marina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Deep Hole you may be interested in

Waterside Inn
Seasonal outdoor pool

Waterside Inn

2.0 star property
8.8 out of 10, Excellent, (1014)
"Thank you : me. And wife happy about this place. ⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️ stars. "
The price is S$89
includes taxes & fees
2 Dec - 3 Dec
Waterside Inn
Key West Cottages
Exterior

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (293)
"I love how quiet and relaxing the property was this time of year. Amazing views. I look forward to returning soon!"
The price is S$155
includes taxes & fees
26 Nov - 27 Nov
Key West Cottages
Comfort Suites Chincoteague Island Bayfront Resort
Indoor pool, outdoor pool, pool umbrellas, pool loungers

Comfort Suites Chincoteague Island Bayfront Resort

2.5 star property
9.6 out of 10, Exceptional, (1011)
" Clean rooms and super nice staff"
The price is S$142
includes taxes & fees
22 Dec - 23 Dec
Comfort Suites Chincoteague Island Bayfront Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Frequently asked questions

Can I find a holiday rental in Deep Hole?

Yes, there are holiday rentals close to the most popular sights in Deep Hole, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Deep Hole has to offer?

Blufin Bungalows & Marina: This holiday home rental outside of Deep Hole is on the beach, and equipped with free WiFi and a TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave.

How many holiday rentals are there in Deep Hole?

Expedia has 81 holiday rentals for your stay in Deep Hole.

What can I see and do in Deep Hole?

While exploring the area, visit family-friendly sights like Maui Jack's Waterpark, or get outside and enjoy nature at Oyster Bay. In the wider area, you’ll find Robert N. Reed Downtown Waterfront Park and Chincoteague National Wildlife Refuge.

What are holiday rentals like in Deep Hole?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Deep Hole. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a family trip.